If you are in the market to buy a new or used boat or outboard engine please keep a few things in mind.
#1 DON'T BUY IT IF IT DOESN'T HAVE THE FEATURES YOU WANT!!
We have seen a lot of things come through here that people have purchased (boats, outboards) and it wasn't quite what they wanted. It's easy to say "oh, I'll just add electric start" "I'll just take the tiller off and hook it up to a steering wheel" "I can have someone install a windlass later" but the truth of the matter is, it's expensive.
It's definitely possible to get rid of tiller and set it up for a remote, it's possible to add electric start, it's all possible but you have to consider the expense of it. You might have got a great deal on that manual start outboard, but it's not a great deal if you have to spend $1000 + to add the electric start later. If it doesn't have power trim and you want to add that it's going to be close to $2000 or more.
If you want an anchor windlass, buy a boat that already has one or is already set up for one because re-engineering the bow of the boat doesn't always look nice after, not to mention the labor hours to do so. You could easily spend $2000-$4000.
#2 SERVICE RECORDS
Ensure that the asking price is reflective of the boat being taken care of. Ask for service records. If the seller says "I do my own service" that usually translates to "I change my own oil". A true service is much more involved than fluid changes; there are many many more control systems that need attention/service.
If you are looking at a stern drive (inboard/outboard) ask about the last time the bellows were replaced. These are often overlooked and could result in a very bad day on the water if they were to fail.
#3 BE WARY OF LOW HOURS
Everyone thinks low hours are great, and on newer boats it is (<5 years old). But if that boat is older and it has low hours that means it's been sitting a lot. Sitting is not good for anything, especially boats. The more they sit the less people feel the need to service them and that's when we run into problems. Impellers take a set and don't pump water as they should, fuel system parts get dried out and leaks can develop, rubber gets weather checked and starts to fail, etc.
#4 GET A PRE-SALE CHECKOUT
It's never a bad idea to have a professional take a look at the boat before you buy it. You might spend $500 but it beats spending 10's of thousands of dollars on a boat only to find out that it needs another $10,000 in repairs due to lack of maintenance. It is also a very handy tool when it comes to negotiating a sale price.
#5 CHECK FOR EASY ACCESS
Look for boats with easy access to engine and other mechanical areas that require maintenance. Limited access may result in higher repair bills. Can you see the starter motor? You don't want a boat that requires a technician to pull your engine out of the boat to replace a starter or a water pump impeller, etc.
#6 CHECK FOR DAMAGE
Look for signs of damage such as paint missing from skeg, damaged propeller, rust or mildew or high water line inside of boat or bilge engine compartment. Look for discolored or melted paint. A prior incident may affect reliability or cost of ownership.
Well cared for boats seem to be a small percentage of the used boats for sale.